Herbicidal method employing meta-anilide urea compounds

ABSTRACT

Meta-anilide urea compositions have the formula:   IN WHICH X and Y are, independently, oxygen and sulfur; R1 is hydrogen or lower alkyl; R2 and R3 are, independently, hydrogen, alkyl, lower alkoxy, haloalkyl, lower alkenyl, cycloalkyl having from 3 to 6 carbon atoms, inclusive, carbalkoxyalkyl, furfuryl, naphthyl, phenyl or substituted-phenyl, inclusive, in which the substituents are halogen, nitro, or lower alkoxy; R4 is hydrogen or lower alkyl; R5 is hydrogen, alkyl, ethyl cycloalkyl, lower alkenyl, halogenated lower alkyl, cycloalkyl having 3 to 6 carbon atoms, inclusive, pinonoyl 2,4-dichlorophenoxymethylene, benzyl, phenyl, or substituted-phenyl in which the substituents are halogen, nitro, lower alkyl, lower alkoxy or trihalomethyl; Z is halogen, lower alkyl, nitro, amino or trifluoromethyl, and m is an integer having a value from 0 to 4, inclusive, provided that when R1, R2, R3 and R4 are each hydrogen, X and Y are each oxygen and m is O, then R5 is other than methyl or ethyl. The compounds are useful as herbicides and they exhibit both preemergence and post-emergence activity. Representative compounds are: 1-(3&#39;&#39;isobutyramidophenyl)-3-methyl urea, 1-cyclohexyl-3-(3&#39;&#39;propionamidophenyl)urea, 1-butyl-3-(3&#39;&#39;-propionamidophenyl) urea, 1-butyl-3-(3&#39;&#39;-isobutyramidophenyl)urea, 1-(3&#39;&#39;-nitrophenyl)-3-(3&#39;&#39;isobutyramidophenyl) urea, 1-N,N-dimethyl-3(pivalamidophenyl)urea, 1-(3&#39;&#39;-propionamidophenyl)-3-n-butyl thiourea, and 1-(3&#39;&#39;-pestafluoropropionamido phenyl)3,3-dimethyl urea.

[ June 17, 1975 1 HERBICIDAL METHOD EMPLOYING META-ANILIDE UREA COMPOUNDS [75] Inventor: Eugene G. Teach, El Cerrito, Calif.

[73] Assignee: Stauffer Chemical Company,

Westport, Conn.

[22] Filed: Sept. 7, 1973 [21] Appl. No.: 396,255

Related U.S. Application Data [60] Division of Ser. No. 180,075, Sept. 13, 1971, Pat. No. 3,790,364, which is a division of Ser. No. 23,021, March 26, 1970, Pat. No. 3,642,891, which is a continuation-in-part of Ser. No. 746,007, July 19, 1968, abandoned, which is a continuation-in-part of Ser. No. 662,573, Aug. 23, 1967, abandoned.

Primary Examiner-James 0. Thomas, Jr. Attorney, Agent, or Firm1-larry A. Pacini; Daniel C. Block; Edwin H. Baker [57] ABSTRACT Meta-anilide urea compositions have the formula:

/Z R on im ge Y in which X and Y are, independently, oxygen and sulfur; R is hydrogen or lower alkyl; R and R are, independently, hydrogen, alkyl, lower alkoxy, haloalkyl, lower alkenyl, cycloalkyl having from 3 to 6 carbon atoms, inclusive, carbalkoxyalkyl, furfuryl, naphthyl, phenyl or substituted-phenyl, inclusive, in which the substituents are halogen, nitro, or lower alkoxy; R is hydrogen or lower alkyl; R is hydrogen, alkyl, ethyl cycloalkyl, lower alkenyl, halogenated lower alkyl, cycloalkyl having 3 to 6 carbon atoms, inclusive, pinonoyl 2,4-dichlorophenoxymethylene, benzyl, phenyl, or substituted-phenyl in which the substituents are halogen, nitro, lower alkyl, lower alkoxy or trihalomethyl; Z is halogen, lower alkyl, nitro, amino or trifluoromethyl, and m is an integer having a value from 0 to 4, inclusive, provided that when R,, R R and R are each hydrogen, X and Y are each oxygen and m is 0 then R,-, is other than methyl or ethyl. The compovno: are useful as herbicides and they exhibit both preemergence and post-emergence activity. Representative compounds are: l-(3-isobutyramidophenyl)-3- methyl urea, l-cyclohexyl-3-( 3 propionamidophenyl )urea, l-butyl-3-( 3 propionamidophenyl) urea, l-butyl-3-( 3 isobutyrarnidophenyl,urea, 1-( 3 -nitrophenyl)-3-( 3 isobutyramidophenyl) urea, l-N,N-dimethyl-3- (pivalamidophenyl)urea, l-(3'-propionamidophenyl)- 3-n-buty1 thiourea, and l-( 3 '-pestafluoropropionamido phenyl)3,3-dimethyl urea.

26 Claims, N0 Drawings 1 HERBICIDAL METHOD EMPLOYING META-ANII JIDE UREA COMPOUNDS I This is a division of application Ser. No. 180,075, filed Sept. 13, 1971, now U.S. Pat. No. 3,790,364, which in turn is a division of then copending application Ser. No. 23,021, filed Mar. 26, 1970, now U.S. Pat. No. 3,642,891, which in turn is a continuation-in-part application of then copending application Ser. No. 746,007, filed July 19, 1968, now abandoned, which in turn is a continuation-in-part application of then copending application Ser. No. 662,573, filed Aug. 23, 1967, now abandoned.

This invention relates to certain novel meta-anilide ureas which are useful herbicides. More specifically, this invention relates to certain substituted organoanilide ureas and to the preparation and utility of the compounds as herbicidesv The compounds of the present invention correspond to the formula:

in which X and Y are independently selected from the group consisting of oxygen and sulfur, R is hydrogen or lower alkyl, R and R are independently selected from the group consisting of hydrogen, alkyl. lower alkoxy, haloalkyl, lower alkenyl, cycloalkyl having from 3 to 6 carbon atoms, inclusive, carbalkoxalkyl, furfuryl, naphthyl, phenyl, substituted-phenyl in which said substituents are selected from the group consisting of halogen, nitro, and lower alkoxy; R is hydrogen or lower alkyl; R, is selected from the group hydrogen, alkyl, ethylcycloalkyl, lower alkenyl, halogenated lower alkyl, cycloalkyl having from 3 to 6 carbon atoms, inclusive, pinonoyl, 2,4-dichlorophenoxymethylene, benzyl, phenyl, substituted-phenyl in which said substituents are selected from the group consisting of halogen. nitro, lower alkyl. lower alkoxy and trihalomethyl; and Z is selected from the group consisting of halogen, lower alkyl, nitro, amino and trifluormethyl, and m is an integer having a value from to 4. inclusive, preferably 0 to 2, inclusive, provided that when R,, R R and R are each hydrogen, X and Y are both oxygen and m is 0, then R, is other than methyl or ethyl.

As employed in this specification. the terms lower alkyl and lower alkoxy preferably include those members of the group containing from 1 to 6 carbon atoms, inclusive, in either a straight chain or a branched chain configuration. Similarly, the term alkyl preferably includes those members of the group containing 1 to 10 carbon atoms, inclusive. The term lower alkenyl preferably includcs those members of the group containing at least one olefinic bond and containing from 2 to 4 carbon atoms, inclusive. The term carbalkoxyalkyl preferably includes those members of theg roup containing from 3 to 6 carbon atoms, inclusive. The term halogen,

as employed herein and in the terms haloalkyl, halogen,

2 halogenated, trihalomethyl, preferably includes fluorine, chlorine and bromine.

The compounds of the present invention are prepared by several methods. Two such methods applicable in preparing the compounds is the condensation between the appropriate meta-amino substituted anilide with either an isocyanate or carbamoyl chloride and also the condensation of the appropriate meta-amino urea and either an acyl halide or acid anhydride. These methods will be further exemplified below. Similarly, an isothiocyanate is employed to prepare the thiourea derivatives. When the unsubstituted amidophenyl urea is prepared a cyanate salt is reacted with the approprite substituted amido aniline. The reactions proceed readily in the liquid phase. The employment of a solvent is also useful, facilitating processing, as well as agitation of the reactants. Solvents such as water, benzene, toluene, acetone, tetrahydrofuran, and the like, are employed. A catalyst may be employed to enhance the reaction although a catalyst is not required. Catalysts such as e.g. dibutyltin dilaurate and anhydrous potassium carbonate and copper powder, are effective catalysts. The-reactions are carried out at temperatures that permit operation in the liquid phase. These temperatures are between about room temperature and reflux temperature of the solvent ifa solvent is employed. Preferably, the reaction mixture is refluxed at an elevated temperature.

Compound of the present invention are prepared i accordance with the following illustrative examples.

EXAMPLE 1 Preparation of l-(3-isobutyramidophenyl)-3-methyl urea Meta-amino isobutyranilide, 12.5g. (0.07 mole), is dissolved in ml. of acetone containing a few drops of dibutyltin dilaurate. Methyl isocyanate, 4.4 g. (0.077 mole), is added to the mixture. The mixture is refluxed for 2 hours. On cooling, the crystalline product is filtered off and dried. There is obtained 8.2 g. (50 percent of theory) of the title compound, m.p. l68-l7lC.

EXAMPLEZ Preparation of l-( 3-Pivalamidophenyl)-3,3-dimethyl Urea Meta-amino pivalanilide 15.4 g. (0.08 moles) is dissolved in 100 ml. of acetone containing 11 g. of finely powdered anhydrous potassium carbonate and a trace of copper powder. Dimethylcarbamoyl chloride 8.6 g. (0.08 mole) is added and the mixture is refluxed for 8 hours with stirring. The solid is filtered off and the acetone is removed under vacuum; The viscous liquid product is triturated with ether and crystallizes. It is washed with water, and 5% hydrochloric acid solution and is dried. There is obtained 12.5 g. (60 percent of theory) of the title compound, m.p. 18ll86C.

EXAMPLE 3 Preparation of l-(3'propionamidophenyl)-3-n-butyl thiourea.

Meta-propionamidoaniline, 8.2 g. (0.05 mole). 'is dissolved in 50 ml. of acetone. To this solution is added 5.8 g. of n-butylisothiocyanate. The resulting mixture is refluxed for 2 hours. After cooling, it is poured on to crushed'ice and washed with water. After filtering, the

product is dried in vacuum. There is obtained 13.8g. (98.5 percent of theory) of the title compound, m.p. 136-138C.

EXAMPLE 4 Preparation of 3'-propionamidophenyl urea Meta-propionamidoaniline, 8.2 g. (9.05 mole) is 'dissolved in 100 ml. of dilute hydrochloric acid solution. Potassium cyanate, 4.1 g. is dissolved in 20 ml. of water and this is added to the above acid solution. The resulting mixture is maintained at 30-40C. for 3 hours. After cooling, the crystals are filtered and washed with water. They are dried further in vacuum. There is obtained 8.9 g. (86 percent of theory) of thetitle compound, m.p. 188-190C.

EXAMPLE 5 Preparation of 1-(3'-butyramidophenyl)-3-methyl urea.

N-Meta-aminophenyl-N-methyl urea, 11.5 g. (0.07 mole) is suspended in 100 ml. of ether and 1 1.1 g. of n-butyric anhydride containing 5 drops of concentrated sulfuric acid is added dropwise. The mixture is heated at reflux for 1 hour. The mixture is cooled and the product filtered off. The product is washed successively with dilute (57:) sodium hydroxide, dilute (5%) HCl, and water and then dried. There is obtained 1 1.2 g. (68 percent of theory) of the title compound, m.p. 158-159C.

EXAMPLE 6 Preparation of 1-(3'-cyclohexanecarboxamidophenyl)-3-methyl urea TA BLE 1 Compound Number X Y R R R R., R,-, Z m.p. C.

1 O O H H CH H 175-179 2 O O H CH CH H 279.5-282 3 o H H 3-Clpheny1 H 209-21 1 4 O O H H 3 H 167-171 5 O O H H C H H 169-173 6 0 0 H H nC H H 169-1705 7 O O H H iC:,H H 168-170 8 O O H H C. ,H H 176-1775 9 O O H H iC;,H; H 184-185 10 O O H H n H H 165-168 1 1 O O H H cyclohexyl H 178-179 12 O O H H phenyl H 211-212 13 O O H H 3NO. .-phenyl H 207-209 14 O O H H n-C,H,, H 151-154 15 O O H H 3.4-diCl henyl H l67-170 16 O O H H CH CO()( .H H 150-152 17 O O H H CH CH=CH5 H 157-160 18 O O H H C,.H,; H 151-154 19 O O H H 4OCH -,phen \'l H 210-21 1 20 O O H H 4-NO ,phenyl H 215-219 21 O O H H nuphthyl H 278-282 22 O 0 H H CH:CH=CH H 175-176 23 O O H H nC,H H 157-1585 24 O O H H cycluhcxfl H 213-217 25 O O H H (,H H 134-136 26 O O H H phenyl H 221-223 27 0 o H H 3Clphenyl H 214-216 28 O O H H 3.4-diCl-phenyl H 218-221 29 O H H 3-NO phenyl H 201-203 30 O H H (H H 164-166 31 O O H H i(';,H; H 179-181 32 O O H H 3(.lphenyl H 218-221 33 O O H CH C a Y H 181-186 34 S O H H n(,H H 136-138 35 S O H H CH H 189-190 36 H H ('H H 181-183 37 O H H 3l\'() ,phcn \'l H 174-177 38 O H (H (H H 169-173 39 0 H CH (H H 178-184 40 O O H (H CH H 133-136 Table 'l Continued ('ompound Number when heated "HHHHHHHHHHHHHHHHH HHHHHHHHHHHHHHHHH OOOOOOOOOOOOOOOOO OOOOOOOOOOOOOOOOO HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH OOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOO OOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOO Other examples of compounds falling within the geformulated into herbicidal compositions and applied as neric formulas presented herein, which are preparable by the aforedescribed procedures and which may be herein illustrated are:

cyclopropane H 0 O CJH phenyl H CH-.CH=CH..

henzyl Herbicidal Screening Tests As previously mentioned, the novel compounds herein described are phytotoxic compounds which are useful and valuable in controlling various plants species. Compounds of this invention are tested as herbicides in the following manner.

Pre-emergence herbicide test. On the day preceding treatment, seeds of seven different weed species are planted in individual rows using one species per row across the width of the flat. The seeds used are hairy crabgrass (Digitaria sanguinalis (L.) Scop.), yellow foxtail (Selaria glauca (L.) Beauv.), watergrass (Echinochloa crusgalli (L.) Beauv.), California red oat (Avena sativa (L.)), redroot pigweed (Amarantlzus retroflexus (L), Indian mustard (Brassica juncea (L.) Coss.) and Curly dock (Rumex Crispus (L.). Ample seeds are planted to give about 20 to 50 seedlings per row, after emergence, depending on the size of the plants. The flats are watered after planting. The spraying solution is prepared by dissolving 50 mg. of the test compound in 3 ml. of a solvent, such as acetone, containing 1% Tween 20 (polyoxyethylene sorbitan monolaurate). The following day each flat is sprayed at the rate of 20 pounds of the candidate compound per 80 gallons of solution per acre. An atomizer is used to spray the solution on soil surface. The flats are placed in a greenhouse at 80F. and watered regularly. Two weeks later, the degree of weed control is determined by comparing the amount of germination and growth of each weed in the treated flats with weeds in several untreated control flats. The rating system is as follows:

no significant injury (-15 percent control) slight injury (25-35 percent control) -H- moderate injury (5565 percent control) +H-= severe injury to death (85-100 percent control) An activity index is used to represent the total activity on all seven weed species. It is the sum of the number of plus marks, so that an activity index of 21 represents complete control of all seven weeds. The results of this test are reported in Table II.

Post-emergence hergicide test. Seeds of five weed species including hairy crabgrass, watergrass, wild oats, Indian mustard, and curly dock and one crop pinto beans (Phaseolus vulgaris), are planted in flats as described above for preemergence screening. The flats are placed in the greenhouse at 7285F. and watered daily with a sprinkler. About 10 to 14 days after planting when the primary leaves of the beam plant are almost fully expanded and the first trifoliate leaves are just starting to form, the plants are sprayed. The spray is prepared by weighing out 50 mg. of the test compound, dissolving it in ml. of acetone containing 1 percent Tween 20 (polyoxy-ethylene sorbitan monolaurate) and then adding 5 ml. of water. The solution is sprayed on the foilage using an atomizer. The spray concentration is 0.5% and the rate would be approximately 20 lb/acre if all of the spray were retained on the plant and the soil, but some spray is lost so it is estimated that the application rate is approximately 12.5 lb/acre.

Beans are used to detect defoliants and, plant growth regulators. The beans are trimmed to two or three plants per flat by cutting off the excess weaker plants several days before treatment. The treated plants are placed back in the greenhouse and care is taken to avoid sprinkling the treated foliage with water for three days after treatment. Water is applied to the soil by means of a slow stream from a watering hose taking care not to wet the foliage.

Injury levels are made and recorded 14 days after treatment. The rating system is the same as described above for the pro-emergence test where (ll-), and (lll-) are used for the different levels of injury and control. The injury symptoms are also recorded. The maximum activity index for complete control of all the species in the post-emergence screening test is 18 which represents the sum of the plus marks obtained with the six plant species used in the test. The herbicide activity indices are shown in Table II.

TABLE II HERBICIDAL ACTlVlTY** SCREENING RESULTS Compound Number Pre-emergence Post-emergence l 18 I8 2 2 0 3 9 ll 4 21 18 5 l6 l8 6 20 18 7 20 18 8 13 15 9 l7 l7 l0 l9 16 ll 21 l8 12 ll l7 l3 0 8 14 21 l8 l5 8 l3 l6 6 l4 l7 l6 l6 l8 0 l0 l9 l2 I3 20 0 12 21 3 O 22 l8 I8 23 20 18 24 0 13 26 4 7 27 0 9 28 6 8 29 5 12 30 l9 18 3I 19 18 32 0 8 33 21 18- 34 9 18 35 0 ll 36 21 I8 37 1 10 38 20 I8 39 20 18 4O l9 l7 4! l7 16 42 20 I8 43 20 I8 44 2O 17 45 20 18 46 l8 I8 47 l3 [8 48 20 I8 49 l9 [6 50 2] 16 5| 20 18 52 21 I7. 53 9 16 54 l2 18 55 20 I8 56 20 17 57 l9 17 58 l9 l8 5) l9 18 60 l5 18 61 9 13 62 5 I2 63 0 4 64 l7 18 65 21 18 66 2] I8 67 8 ll 21 18 TABLE ll-Continued Compound Number Pre'emergence Post-emergence 69 21 18 70 18 18 71 6 13 72 10 17 73 4 74 7 17 18 7 4 16 77 15 18 78 9 18 79 5 14 80 18 18 g1 19 18 11 1 11 8 19 18 114 14 18 11 18 86 4 11 87 2 11 88 21 18 89 0 9 90 I ll 91 7 14 92 20 17 93 21 18 94 21 18 95 17 14 96 11 16 97 14 18 9 21 18 99 15 17 100 20 18 101 21 18 102 17 18 103 21 18 104 0 5 105 10 17 106 0 5 107 7 18 108 0 5 109 0 10 110 20 18 111 17 18 112 l9 I8 113 20 18 114 20 18 115 21 18 116 0 6 117 21 18 118 21 18 119 21 18 120 19 18 121 19 18 122 15 17 123 21 18 124 l 18 125 16 18 126 16 18 127 12 16 128 19 18 129 18 18 130 19 18 131 18 16 132 12 14 133 12 14 134 11 16 135 I4 12 6 11 13 137 10 12 138 3 10 139 15 18 140 l5 I8 141 15 16 142 l7 I8 143 I I8 144 17 14 145 18 18 146 5 II 147 21 18 148 21 18 149 21 18 150 21 18 151 21 18 152 21 153 21 I8 154 21 18 155 21 I8 156 21 I8 TABLE ll-Continued HERBlClDAL ACTIVITY SCREENING RESULTS "2| 85-10(1'4 control of all seven plant species tested prc-emergencc. 18 85-]0071 control of all six plant species tested post-emergence.

The new compounds of the present invention are used as pre-emergence or post-emergence herbicides and are applied in a variety of ways at various concentrations. In practice, the compounds are formulated with an inert carrier, utilizing methods well-known to those skilled in the art, thereby making them suitable for application as dusts, sprays, or drenches and the like in the form and manner required. The mixtures can be dispersed in water with the aid of a wetting agent or they can be employed in organic liquid compositions, oil and water, water in oil emulsions, with or without the addition of wetting, dispersing or emulsifying agents. The amount applied depends upon the nature of the seeds or plants to be controlled and the rate of application varies from approximately 1 to approximately 50 pounds per acre. One particularly advantageous way of applying the compound is a narrow band along a row crop straddling the row. In practice, the compounds are formulated with an inert carrier utilizing methods well known to those skilled in the art, thereby making them suitable for particular application.

The phytotoxic compositions of this invention are applied to the plants in the conventional manner. Thus, the solid and liquid compositions can be applied to the plant by the use of, for example, power-dusters, boom and hand sprayers and spraydusters. The compositions can also be applied from airplanes as a dust or a spray because they are effective in very low dosages. ln order to modify or control growth of germinating seeds or emerging seedlings, as a typical example, the dust and liquid compositions are applied to the soil according to conventional methods and are preferably distributed in the soil to a depth of at least one-half inch below the soil surface. It is necessary that the phytotoxic compositions be admixed with the soil particles and these compositions can be applied merely by spraying or sprinkling the surface of the soil. The phytotoxic compositions of this invention can also be applied by addition to irrigation water supplied to the field to be treated. This method of application permits the penetration of the compositions into the soil as the water is absorbed therein. Dust compositions, granular compositions or liquid formulations applied to the surface if the soil can be distributed below the surface of the soil by conventional means such as discing, dragging or mixing operations.

The phytotoxic compositions of this invention can also contain other additaments, for example, fertilizers, pesticides and the like, used as adjuvant or in combination with any of the above-described adjuvants. Other phyototoxic compounds useful in combination with the above-described compounds include for example, 2,4-dichlorophenoxyacetic acids, 2,4,5-trichlorophenoxyacetic acid 2-methyl-4-chlorophenoxyacetic acid and the salts, esters and amides thereof; triazine derivatives, such as 2,4-bis (3-methoxypropylamino)- 6-methylthio-S-triazine; 2-chloro-4 ethylamino-6-isopropylamino-S-triazine, and 2-ethylamino-4- isopropylamino-6-methylmercapto-S-triazine, urea derivatives, such as 3-(3,4-dichlorophenyl)-l,l-dimethyl urea and 3-(p-chlorophenyl)-l,l-dimethyl urea and acetamides such as N, N diallyl a -chloroacetamide, N-(a-chloroacetyl) hcxamethylene imine, and N,N-diethyl-a-bromacetamidc, and the like; benzoic acids such 3-amino-2,5-dichlorobenzoic and; thiocarbamates, such as S-propyl dipropylthiocarbamate; S-ethyl-dipropylthiocarbamate, S-ethyl-cyclohexylethyl-thiocarbamate, S-ethyl hexahydrol H-azepinel carbothioate and the like. Fertilizers useful in combination with the active ingredients include for example, ammonium nitrate, urea and superphosphates. Other useful additaments include materials in which plant organisms take root and grow such as compost, manure, humus, sand and the like.

The concentration of a compound of the present invention, constituting an effective amount in the best mode of administration in the utility disclosed is readily determinable by those skilled in the art. Various changes and modifications are possible without departing from the spirit and scope of the invention described herein and will be apparent to those skilled in the art to which it pertains. it is accordingly intended that the present invention shall only be limited by the scope of the claims.

What is claimed is:

1. A method for controlling the growth of vegetation which comprises applying to the area where control of said vegetative growth is desired, a growth controlling amount of a compound having the formula ll R NHCN\R Nae-R 0 in which X is selected from the group consisting of oxygen and sulfur, R is selected from the group consisting of hydrogen, alkyl, and lower alkoxy, R is selected from the group consisting of alkyl, alkenyl and cycloalkyl, R is selected from the group alkyl, and halogenated lower alkyl, provided that when X is oxygen and R and R are each alkyl then R is other than hydrogen.

2. The method according to claim 1 in which X is oxygen, R is hydrogen, R is eycloalkyl having 3 to 6 carbon atoms, inclusive, and R is alkyl.

3. The method according to claim 2 in which R is cyclohexyl and R is ethyl.

4. The method acording to claim 2 in which R is cyclohexyl and R is tert-butyl.

5. The method according to claim 2 in which R, is cyclohexyl and R is l,l-dimethylbutyl.

6. The method according to claim 1 in which X is oxygen, R R and R are each alkyl.

7. The method according to claim 6 in which R is methyl, R is methyl and R is tert-butyl.

8. The method according to claim 6 in which R; is methyl, R is methyl and R is n-propyl.

9. The method according to claim 1 in which X is sulfur, R is hydrogen, R and R are each alkyl.

10. The method according to claim 9 in which R is methyl and R is ethyl.

11. The method according to claim 9 in which R is n-butyl and R is ethyl.

12. The method according to claim 1 in which X is oxygen, R and R are each alkyl, and R is a halogenated lower alkyl.

13. The method according to claim 12 in which R is methyl, R is methyl, and R is trichloromethyl.

14. The method according to claim 12 in which R is methyl, R is methyl, and R is trifluoromethyl.

15. The method according to claim 12 in which R is methyl, R is methyl, and R is pentafluoroethyl.

16. The method according to claim 1 in which X is oxygen, R is hydrogen, R is lower alkenyl, and R is alkyl.

17. The method according to claim 16 in which R is allyl and R is tert-butyl.

18. The method according to claim 16 in which R, is allyl and R is l-methylbutyl.

19. The method according to claim 16 in which R is allyl and R is l,l-dimethylbutyl.

1 20. The method according to claim 16 in which R is allyl and R is isopropyl.

21. The method according to claim 1 in which X is oxygen, R is lower alkoxy, R is alkyl and R is alkyl.

22. The method according to claim 21 in which R is methoxy, R is methyl and R is ethyl.

23. The method according to claim 21 in which R is methoxy, R is methyl and R is t-butyl.

24. The method according to claim 21 in which E is methoxy, R is methyl and R is neopentyl.

25. The method according to claim 21 in which R is methoxy, R is methyl and R is l-methylbutyl.

26. The method according to claim 21 in which R is methoxy, R is methyl and R is l,l-dimethylbutyl. 

1. A METHOD FOR CONTROLLING THE GROWTH OF VEGETATION WHICH COMPRISES APPLYING TO THE AREA WHERE CONTROL OF SAID VEGETATIVE GROWTH IS DESIRED, A GROWTH CONTROLLING AMOUNT OF A COMPOUND HAVING THE FORMULA
 2. The method according to claim 1 in which X is oxygen, R2 is hydrogen, R3 is cycloalkyl having 3 to 6 carbon atoms, inclusive, and R5 is alkyl.
 3. The method according to claim 2 in which R3 is cyclohexyl and r5 is ethyl.
 4. The method acording to claim 2 in which R3 is cyclohexyl and R5 is tert-butyl.
 5. The method according to claim 2 in which R3 is cyclohexyl and R5 is 1,1-dimethylbutyl.
 6. The method according to claim 1 in which X is oxygen, R2, R3 and R5 are each alkyl.
 7. The method according to claim 6 in which R2 is methyl, R3 is methyl and R5 is tert-butyl.
 8. The method according to claim 6 in which R2 is methyl, R3 is methyl and R5 is n-propyl.
 9. The method according to claim 1 in which X is sulfur, R2 is hydrogen, R3 and R5 are each alkyl.
 10. The method according to claim 9 in which R3 is methyl and R5 is ethyl.
 11. The method according to claim 9 in which R3 is n-butyl and R5 is ethyl.
 12. The method according to claim 1 in which X is oxygen, R2 and R3 are each alkyl, and R5 is a halogenated lower alkyl.
 13. The method according to claim 12 in which R2 is methyl, R3 is methyl, and R5 is trichloromethyl.
 14. The method according to claim 12 in which R2 is methyl, R3 is methyl, and R5 is trifluoromethyl.
 15. The method according to claim 12 in which R2 is methyl, R3 is methyl, and R5 is pentafluoroethyl.
 16. The method according to claim 1 in which X is oxygen, R2 is hydrogen, R3 is lower alkenyl, and R5 is alkyl.
 17. The method according to claim 16 in which R3 is allyl and R5 is tert-butyl.
 18. The method according to claim 16 in which R3 is allyl and R5 is 1-methylbutyl.
 19. The method according to claim 16 in which R3 is allyl and R5 is 1,1-dimethylbutyl.
 20. The method according to claim 16 in which R3 is allyl and R5 is isopropyl.
 21. The method according to claim 1 in which X is oxygen, R2 is lower alkoxy, R3 is alkyl and R5 is alkyl.
 22. The method according to claim 21 in which R2 is methoxy, R3 is methyl and R5 is ethyl.
 23. The method according to claim 21 in which R2 is methoxy, R3 is methyl and R5 is t-butyl.
 24. The method according to claim 21 in which E2 is methoxy, R3 is methyl and R5 is neopentyl.
 25. The method according to claim 21 in which R2 is methoxy, R3 is methyl and R5 is 1-methylbutyl.
 26. The method according to claim 21 in which R2 is methoxy, R3 is methyl and R5 is 1,1-dimethylbutyl. 